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Chalcogen Bonding Catalysis of the Cloke-Wilson Rearrangement
Xinglong Yuan1, Lintao Bao1, Zhiguo Zhao1
1School of Chemistry and Chemical Engineering Key Laboratory of the Colloid and Interface Chemistry, Ministry of Education, Shandong University, Jinan, 250100, P. R. China.
Abstract:
The Cloke-Wilson rearrangement is an important method to construct heterocycles which was conventionally facilitated by strong Lewis acids, Brønsted acids and Lewis bases. A weak interaction catalysis approach to the Cloke-Wilson rearrangement remains a challenging topic and yet no example is reported. Herein, a chalcogen bonding catalysis method to achieve the Cloke-Wilson rearrangement is described that involves activation of carbonyl cyclopropanes by double Se⋅⋅⋅O interactions. This chalcogen bonding catalysis approach afforded a wide range of dihydrofurans with good yields, thus establishing an alternative strategy to catalyze the Cloke-Wilson rearrangement.
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